Methyl iodide → HCID 86700460, compound

HRID 879651Notes

Reaction equation

HRID 879651 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([I:11])=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1.[C:12]([O-])([O-])=O.[Cs+].[Cs+].CI.ClC1C=CC2C(=C(I)N(C)N=2)N=1>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([I:11])=[N:9][N:10]([CH3:12])[C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86700461HCID 86700461, compoundHCID 178477913HCID 178477913, compound

Product 1

HCID 86700460HCID 86700460, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-3-iodo-1H-pyrazolo[4,3-b]pyridine (102 mg, 0.365 mmol) in DMF (3 mL), was added Cs2CO3 (237 mg, 0.73 mmol), MeI (35 μL, 0.55 mmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with EtOAc and water, the organic phase was dried over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-50% EtOAc in hexanes to give the product containing the isomer 5-chloro-3-iodo-2-methyl-2H-pyrazolo[4,3-b]pyridine (in about 1.5:1 ratio). LCMS-ESI+: calc'd for C7H5Cl1N3: 293.9 (M+H+); Found: 294.1 (M+H+).

Workup

  1. dry with materialthe organic phase was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified by silica gel column
  5. washeluting by 0-50% EtOAc in hexanes
  6. customto give the product

Sources & evidence

ORD record
ord-92e3529a25d749df913b18202066b782
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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